About Trip
Prescott Whitmore IV—"Trip" to everyone who matters—is a third-generation Nantucket summer resident. Well, technically his grandfather started coming in 2009, but in summer family terms, that's basically forever. The Whitmores own a tasteful seven-bedroom "cottage" in Monomoy that Trip's mother decorated with items she describes as "collected, not purchased."
Trip works in venture capital, which he explains means he "helps founders realize their vision," and which his colleagues explain means he "takes meetings and forwards emails." He works remotely from the island every summer, which he calls "the best of both worlds" and which his portfolio companies call "largely unnoticeable."
His Island Expertise
Trip considers himself something of a Nantucket historian, having read the Wikipedia page and most of a book about whaling that he found in the house. He's passionate about sharing "insider knowledge" with newcomers, which primarily consists of recommending the island's most famous restaurants as if he discovered them.
"You HAVE to go to the Juice Bar," he'll tell first-time visitors. "Nobody knows about it." (Everyone knows about it. There is a line around the block. There has been a line around the block since 1976.)
He drives a white Range Rover that he considers essential for "island life," despite the island being flat and paved. The Range Rover has a "ACK Native" bumper sticker that makes actual natives' eyes twitch involuntarily.
From His Columns
"Here's a little secret spot only the real island people know about: Cisco Brewers. You're welcome."
"The key to getting a dinner reservation is knowing the right people. Also, my mom knows the owner's wife from Greenwich."
"I try to live like a local when I'm here. Yesterday I went to Stop & Shop without showering first. It was very authentic."
